Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

HRID 50235

反応式

HRID 50235 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH3:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:9])[S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[C:12]([N+:21]([O-:23])=[O:22])[CH:13]=2)(=[O:18])=[O:19])[CH2:4][CH2:3]1

参加物

4

反応物 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 5663231-Methyl-4-(methylamino)piperidine

生成物 1

HCID 113714564-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 2.2 mL (15 mmol) of 1-methyl-4-methylaminopiperidine in 60 mL pyridine, 3.8 g (15 mmol) of 4-chloro-3-nitrobenzenesulfonic acid chloride were added, in batches, whilst cooling with ice. The mixture was then stirred for two hours with cooling, then evaporated to dryness, the residue was mixed with about 50 mL of water and made alkaline with concentrated ammonia whilst stirring vigorously. The crude product precipitated was suction filtered and purified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol). Yield: 1.6 g (31% of theory), C13H18ClN3O4S (347.8); Rf value: 0.19 (silica gel; dichloromethane/ethanol=19:1).

後処理

  1. temperaturewhilst cooling with ice
  2. temperaturewith cooling
  3. customevaporated to dryness
  4. additionthe residue was mixed with about 50 mL of water
  5. stirringwhilst stirring vigorously
  6. customThe crude product precipitated
  7. filtrationfiltered
  8. custompurified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol)

出典と根拠

ORDレコード
ord-a4b92adeb6194e9899e79b37a3d3ec15
出典データセット
uspto-grants-2004_03
特許番号
US06710055B2

関連ノート

読み込み中…